By today’s standards, Frank Sinatra comes off as obtuse and dusty. The image of a tuxedoed old man bobbing across a stage crooning sanitized jazz standards smacks more of mealy-mouthed nostalgia than anything else, and nostalgia is by its nature almost always conservative.

Indeed, in 1985 Sinatra received the Presidential Medal of Freedom from Ronald Reagan — whom he supported. Conferring the medal on Sinatra, Reagan declared: “His love of country, his generosity for those less fortunate, make him one of our most remarkable and distinguished Americans.”

It’s a politico-artistic association that, however cringeworthy, maintains an internal logic. Two old white men shaking hands; your uber-conservative grandfather sings Reagan’s praises and Sinatra’s songs. It would be easy then to merely shrug at the fact that Sinatra would have turned one hundred this month.

But viewing cultural history through the lens of the present has obvious shortcomings. If we go back far enough we can always see the potential for a different ending: back to before Sinatra parted ways with the Democrats for swinging “too left” by nominating George McGovern in 1972, before he was pushing for the desegregation of Las Vegas casinos and reportedly making Martin Luther King Jr. weep with his version of “Ol’ Man River.” Back to when he was denied security clearance to perform for the troops in Korea.

The reason the US government denied Sinatra authorization (despite having supported the hawkish Harry Truman in 1948) was straightforward. The Korean War represented a shot across the bow for the wider, decades-long Cold War and Sinatra, though never a member, had been far too friendly with the Communist Party.

From 1944 to 1948, Sinatra lent his name, money, and presence to countless Communist-affiliated, antiracist, antifascist, and internationalist groups: the American Crusade to End Lynching, the Joint Anti-Fascist Refugee Committee, the Free Italy Society.

He supported left cultural publications such as L’Unita del Popolo (an Italian-language biweekly), and in 1945 did a full-page interview mapping out his social and political beliefs for the Daily Worker. The following year, the Communist magazine New Masses honored Sinatra — along with W.E.B. DuBois, Duke Ellington, Paul Robeson and others — for his “contributions towards [the creation of] an America for all peoples.”

Gerald Meyer, in an article on Sinatra’s left affiliations for Science & Society, argues that “Sinatra’s early life predisposed him to the Left.” His parents were both the children of immigrants at a time when Italians had yet to be fully integrated into American society. Hoboken, his hometown, had a reputation as consummately blue collar, and Sinatra grew up in the toughest and most diverse part of the city.

In the Daily Worker interview he told writer and poet Walter Lowenfels: “I was brought up in a tenement . . . in a very poor neighborhood. It was a real melting pot, a cross-section of every racial group in the country.” Few political forces were as genuinely interested in relating to all these people — or had the resources to do so — as the Communist Party.

Sinatra’s — at times quite ardent — involvement with the Left coincided with the peak of the Popular Front, that era in politics and culture that, as Michael Denning writes in The Cultural Front, signified a broad and powerful social-democratic consciousness among the American people as a whole.

Naturally, the left organization most capable of influencing this moment was the Communist Party, but the reach of the Popular Front went far beyond its formidable ranks. Kept buoyant by a mass influx of workers into the American labor movement and a wave of organizing drives, strikes, and other workplace struggles, working people weren’t just pushing back against the official cultural-political landscape at the time. They were showing their potential to dramatically reshape it.

All of this took place at a time when technology was beginning to directly foster and shape popular culture. The mechanical reproducibility of art, music, and performance, the explosion of popularity in film and radio, meant that culture and the ideas within it had become more easily communicable than ever before. This, coupled with an expansion of the American state’s cultural infrastructure, made it possible for more workers to make a living as singers, entertainers, writers, or artists.

Sinatra was one of these. And in the broader context of this moment, the Communist Party and the Popular Front were both uniquely positioned to achieve an impressive degree of cultural hegemony. In this sense Sinatra can be understood as embodying possibility — one example of what it might look like when the far left is able to shape the parameters of cultural expression.

The House I Live In

It is difficult to exaggerate the breadth of left-wing and progressive groups that existed for cultural workers in the later days of the Popular Front. By World War II, Roosevelt’s New Deal programs had expanded to include robust works programs for painters, sculptors, actors, directors, writers, and musicians.

This had a knock-on effect on the ideas and consciousness of artists themselves, many of whom already displayed left sympathies or would very soon. Groups and publications were founded and advocated for better pay and working conditions for cultural workers (including the right to organize) and in many cases tied their own struggles to those against fascism and racism.

One of these groups was the Independent Citizens Committee of the Arts, Sciences, and Professions (ICCASP). ICCASP was, in essence, a big-tent organization of left-leaning notables and celebrities who lent credence to progressive causes: free speech, racial equality and, after the end of World War II, campaigns against the atomic bomb.

Starting in 1946, Sinatra was one of ICCASP’s vice presidents. Other leading members included Albert Einstein, James Cagney, Bette Davis, Orson Welles, Thomas Mann, and Langston Hughes. ICCASP wielded a significant amount of influence among well-known creatives and was proof that Popular Front ideas reached both the small community playhouses of Anytown, USA and the minds of some of Hollywood’s biggest stars.

Though he performed and spoke at countless progressive fundraisers, Sinatra’s only foray into recording on behalf of the Left during this time was The House I Live In, a ten-minute short film made in 1945 that starred Sinatra and was written by CP member Albert Maltz. The music for the title song was composed by Earl Robinson and the lyrics by Abel Meeropol (of “Strange Fruit” fame). Both Robinson and Meeropol were also Communists.

The House I Live In is quintessential Popular Front, in both the good and the bad. The plot involves Sinatra (playing himself) going on a smoke break outside the studio only to be interrupted by a gang of boys chasing another boy down the street because “We don’t like his religion.” Sinatra, through both talk and song, convinces the gang of boys to be more tolerant, that the American way is inclusive. He asks, in song, “What is America to me?”

The house I live in, a plot of earth, a street
The grocer and the butcher, and the people that I meet
The children in the playground, the faces that I see
All races and religions, that’s America to me

The place I work in, the worker by my side
The little town or city where my people lived and died
The “howdy” and the handshake, the air of feeling free
And the right to speak my mind out, that’s America to me

The boys end up convinced, and walk way as friends.

This is a distillation of the “Communism is twentieth-century Americanism” line that the CP brandished before and during World War II. Patriotic but strongly social-democratic, populist, and antiracist in character, it not so subtly hints at the idea that the best possible America is one that belongs to working people.

Despite Sinatra’s impassioned singing and commendable acting, The House I Live In is pure schmaltz. A fairly trite piece of filmmaking, the plot is more parable than story and the title song — quite intentionally — is the best part. One walks away from the film with the distinct sense that art loses something when it is placed solely at the subservience of a political cause, rather than allowing art and politics to interact of their own accord.

Yet one shouldn’t completely dismiss the film or the song. At the 1946 Academy Awards, The House I Live In was presented with an Honorary Oscar and in 2007, it was added to the Library of Congress’s list of historically significant films. Both achievements reflect the powerful influence of the Communist Party — how much it shaped artistic expression, how the possibilities for cultural production can expand and contract based on what political valences are tugging on it.

Moreover, the message of the film’s title song was not always welcome; at least once, Sinatra put himself in harm’s way to perform the song. In November 1945, Sinatra traveled to Froebel High School in Gary, Indiana. White students had walked out of classes to protest integration (Froebel’s Parent Teacher Association was, not coincidentally, led by the wife of the Communist Party’s local organizer, and Sinatra would later claim the student strike had been instigated by a former leader of the Nazi German-American Bund).

At Froebel, Sinatra faced a hostile crowd. The shouts and jeers were apparently so bad that at one point, the slightly-built singer stood up and claimed “I can lick any son of a bitch in this joint.” As the Chicago Daily Defender reported:

Sinatra, blue suit and red bow-tie, five feet ten inches tall and 138 pounds, the heavyweight in the hearts of the teenagers, stepped to the stage amid weeping, some fainting, much crying, and said, “You should be proud of Gary, but you can’t stay proud by pulling this sort of strike. . .”

When he described his own racial background and told how he was called a “dirty little Guinea,” the students yelled in horror, “No, no, no!”

When he sang “The House I Live In,” a strange silence fell upon his normally noisy worshippers and for once they screamed only when the song ended.

Sinatra’s appearance didn’t end the strike but it did make clear which side he was on.

How Sinatra Was Lost

Today there is a certain shallow perspective of art associated with the Popular Front, one that says far more about the contemporary lens through which the era is viewed than the actual political moment itself. Most regard art from the period as politically important but artistically mundane.

It’s true that much of the best-known cultural expression of the time could be heavy on “message” but light on aesthetic innovation and it’s also not too far-fetched to tie the worst examples of this to the Communist Party’s own didactic, two-dimensional outlook on the arts, which itself took a cue from the “socialist realist” cultural policy of Moscow.

However, to say this was the whole story misses the mark, taking into account neither the still relatively novel position that the culture industry occupied at the time nor the sheer breadth of diversity in art that the Popular Front cleared the way for.

Yes, there were pop acts that aspired to little more than the most mainstream sensibilities, but there were also far more experimental artists and movements working in the same broad tent or that, at the very least, got their start in it.

Earl Robinson had studied under the German avant-garde composer and communist Hanns Eisler. Abel Meeropol ran in the same circles as many of the most innovative poets and writers of the modernist left wing. Without the swing and big band of Cab Calloway, there would have been none of the improvisatory breakthroughs in the bebop of Dizzy Gillespie. (And indeed, Gillespie’s second major professional job was as a member of Calloway’s orchestra.) And more broadly, the aesthetic importance of African-American jazz in popular culture — including Sinatra’s music — should not be understated.

Taking all of this in, one can start to trace the significance of “the laboring of American culture.” If ordinary people were to be in control of their work, then they could redefine it. If art was work, then the possibilities of a culture controlled by workers would in turn be endless. The artists promoted, the themes they presented, the way the songs could sound, even the parameters of taste and quality — all could be drastically shifted when the radical becomes popular.

It is possible then that Sinatra might have ended up on a different artistic road, one that didn’t result in the singer becoming a parody of himself? It’s impossible to definitively answer that question but it’s also very conceivable. However, a different trajectory for Sinatra would have required the Communist Party to be a qualitatively different organization.

By the end of World War II, the CP had long since effectively ceased to be a revolutionary organization. Its decision to hang its fortunes on Roosevelt — including support for military actions in Europe and the South Pacific and the shameful internment of Japanese Americans — had fundamentally compromised its ability to act independently from the US political machine.

Put differently, the Communist Party had — in large part at the behest of Moscow — abused the balance between political influence and political credibility. It had numbers and mainstream clout, but when the tides turned, it did not have the wherewithal or capacity to effectively take on McCarthyism.

Though Sinatra was never called to testify in front of the House Un-American Activities Committee, newspaper reporters had started to publish pieces criticizing his “penchant to veer to portside.” Leftists with whom he had worked in the past — Albert Maltz, Earl Robinson — were blacklisted and the vibrant cultural spaces that radicals had spent two decades building either dwindled or were outright crushed. Sinatra’s career began to go into nose dive.

In 1947, Sinatra had been one of the most vocal supporters of the Hollywood Ten against HUAC’s attacks, but by April 1948, he was recording Italian-language public service announcements urging listeners to vote against the Italian Communist Party in the country’s upcoming elections. Despite his dramatic political about-face it would still take until well into the 1950s for Sinatra’s career to recover.

Sinatra’s turn wasn’t uncommon among fellow travelers, and while his support for civil rights would last until the sixties, his rightward drift continued. His art deteriorated at the same time. The 1950s saw him dabbling in darker, more understated material (which arguably reflected a kind of existential dread running through American society and perhaps might have even said something about the artist’s post-left state of mind) but his output became more and more stultified.

By the 1970s, Sinatra’s musical style had become frozen in time, a kind of simulacrum of how jazz standards are “supposed” to sound. “The House I Live In,” which had long ago disappeared from his repertoire for being too emblematic of his leftist past, suddenly reappeared. Only now it was being performed at the White House for Richard Nixon, at Reagan’s 1985 inauguration, and in support of the troops during the 1991 Persian Gulf War.

What started as a case study in how popular culture could be redefined through political engagement and empowerment had become a long death march into the anodyne. The anodyne makes a sterling accompaniment to solipsistic longings for “the way things were,” but it can’t yield much in the way of a future. That’s because “the way things were” never was. Nor did they have to end up the way they did.

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By today’s standards, Frank Sinatra comes off as obtuse and dusty. The image of a tuxedoed old man bobbing across a stage crooning sanitized jazz standards smacks more of mealy-mouthed nostalgia than anything else, and nostalgia is by its nature almost always conservative. Indeed, in 1985 Sinatra received the Presidential Medal of Freedom from Ronald […]

By today’s standards, Frank Sinatra comes off as obtuse and dusty. The image of a tuxedoed old man bobbing across a stage crooning sanitized jazz standards smacks more of mealy-mouthed nostalgia than anything else, and nostalgia is by its nature almost always conservative. Indeed, in 1985 Sinatra received the Presidential Medal of Freedom from Ronald […]

By today’s standards, Frank Sinatra comes off as obtuse and dusty. The image of a tuxedoed old man bobbing across a stage crooning sanitized jazz standards smacks more of mealy-mouthed nostalgia than anything else, and nostalgia is by its nature almost always conservative. Indeed, in 1985 Sinatra received the Presidential Medal of Freedom from Ronald […]